A naphthalene-based Al3+ selective fluorescent sensor for living cell imaging

An efficient fluorescent Al(3+) receptor, N-(2-hydroxy-1-naphthalene)-N'-(2-(2-hydroxy-1-naphthalene)amino-ethyl)-ethane-1,2-diamine (L) has been synthesized by the condensation reaction between 2-hydroxy naphthaldehyde and diethylenetriamine. High selectivity and affinity of L towards Al(3+) in ethanol (EtOH) as well as in HEPES buffer at pH 7.4, makes it suitable to detect intracellular Al(3+) with fluorescence microscopy. Metal ions, viz. Li(+), Na(+), K(+), Mg(2+), Ca(2+), Mn(2+), Co(2+), Ni(2+), Cu(2+), Zn(2+), Ag(+), Cd(2+), Hg(2+) and Pb(2+) do not interfere. The lowest detection limit for Al(3+) is 3.0 × 10(-7) M and 1.0 × 10(-7) M in EtOH and HEPES buffer respectively.     

Interaction of a Schiff-base fluorescent sensor with Al3+: experimental and computational studies

A fluorescent Al³⁺ chemo-sensor, 1-phenyl-3-methyl-5-hydroxypyrazole-4-acetone-(3′,4′-dimethylpyrrole-2′-formyl) hydrazone (L), has been synthesized and characterized. L can detect Al³⁺ in ethanol solution with a significant fluorescence enhancement of a turn-on ratio over 155-fold due to the formation of a 1?:?1 complex which is based on the molar ratio between L and Al³⁺ ions, and the 1?:?1 stoichiometric complexation can be obtained from density functional theory calculations. No significant interference of other metal ions such as Na⁺, K⁺, Mg²⁺, Ca²⁺, Ni²⁺, Zn²⁺, Cd²⁺, Co²⁺, Cu²⁺, Fe³⁺, Cr³⁺, Pb²⁺, and Ag⁺ was found. The detection limit for Al³⁺ was 5?×?10^?9?M in ethanol.     

A selective and ratiometric bifunctional fluorescent probe for Al3+ ion and proton

A new bifunctional probe based on a pyrene-amino acid conjugate for the differential response of Al(3+) and H(+) was demonstrated for the first time. Interestingly, two solvent-dependent sensing mechanisms for Al(3+), which feature a ratiometric change from excimer to monomer in CH(3)OH and a turn-on response in water, are also disclosed.     

A selective fluorescent probe for carbon monoxide imaging in living cells

A genetically encoded fluorescent probe is capable of selectively detecting carbon monoxide inside living cell. The probe, named COSer (CO sensor), consists of a circularly permuted yellow fluorescent protein (cpYFP) inserted into the regulatory domain of the bacterial CO-sensing protein, CooA, which gives the probe its selective CO-binding property.     

A selective reaction-based fluorescent probe for detecting cobalt in living cells

A reaction-based strategy exploiting cobalt-mediated oxidative C-O bond cleavage affords a selective turn-on fluorescent probe for paramagnetic Co(2+) in water and in living cells.     

A selective near-infrared fluorescent probe for singlet oxygen in living cells

A selective near-infrared fluorescent probe (His-Cy), which features a fast response to (1)O(2) with high sensitivity and selectivity, was designed, synthesized and applied to bioimaging.     

BODIPY based colorimetric fluorescent probe for selective thiophenol detection: theoretical and experimental studies

A BODIPY-based selective thiophenol probe capable of discriminating aliphatic thiols is reported. The fluorescence off-on effect upon reaction with thiol is elucidated with theoretical calculations. The sensing of thiophenol is associated with a color change from red to yellow and 63-fold enhancement in green fluorescence. Application of the probe for selective thiophenol detection is demonstrated by live cell imaging.     

A fluorescent probe for Hg2+sensing in solutions and living cells with a wide working pH range简

In this paper, 2-carboxybenzaldehyde rhodamine B thiohydrazine(1) was synthesized and developed as a fluorescent probe to recognize Hg2+in DMF/H2 O(1:9, v/v) solution with high selectivity. The probe can be applied to the quanti?cation of Hg2+with a linear concentration range covering from 1.0×10-7mol/L to 1.0×10-5mol/L(R2= 0.9985) and a detection limit of 4.2×10-8mol/L. The experiment results show that the response of probe 1 to Hg2+is pH-independent in a wide range from 4.0 to 9.0. Moreover, the probe 1 exhibits excellent selectivity toward Hg2+over other common metal cations. Most importantly, the probe can be employed to monitor Hg2+in living cells using fluorescent imaging technique with satisfied results.     

A new highly sensitive and selective fluorescent probe for Hg2+ and its application in living cells

Abstract

A new coumarin-based probe (HgP) with two “S” groups was designed and synthesized The probe HgP exhibited a fast response time (<2?min) and high selectivity (DL, 2.2?×?10^?7?mol/L). Furthermore, its capability of biological application was stu died, and the results showed that it could be applied to recognize Hg²⁺ in living cells (HK2 cells).     

A highly selective fluorescent probe for the detection and imaging of peroxynitrite in living cells

We have found a specific reaction between ketone 1 and peroxynitrite (ONOO-), rather than other reactive oxygen species and reactive nitrogen species generated in the biological system. On the basis of this reaction, we have successfully developed a new fluorescent probe HKGreen-1, which is highly selective for the detection of peroxynitrite in living cells. Before the oxidation with peroxynitrite, the dichlorofluorescein part is masked and the probe is nonfluorescent. However, upon reaction with peroxynitrite, the fluorophore is released, resulting in strong enhancement in fluorescence intensity.     

A highly sensitive and selective fluorescent probe for trivalent aluminum ion based on rhodamine derivative in living cells

A rhodamine spirolactam derivative (1) is developed as a colormetric and fluorescent probe for trivalent aluminum ions (Al³⁺). It exhibits a highly sensitive “turn-on” fluorescent response toward Al³⁺ with a 70-fold fluorescence intensity enhancement under 2 equiv. of Al³⁺ added. The probe can be applied to the quantification of Al³⁺ with a linear range covering from 5.0 × 10⁻⁷ to 2.0 × 10⁻⁵ M and a detection limit of 4.0 × 10⁻⁸ M. Most importantly, the fluorescence changes of the probe are remarkably specific for Al³⁺ in the presence of other metal ions, which meet the selective requirements for practical application. Moreover, the experiment results show that the response behavior of 1 towards Al³⁺ is pH independent in neutral condition (pH 6.0–8.0) and the response of the probe is fast (response time less than 3 min). In addition, the proposed probe has been used to detect Al³⁺ in water samples and image Al³⁺ in living cells with satisfying results.     

Naphthalene dianhydride based selective detection targetable fluorescent probe for monitoring exogenous Iron in living cells

A green emissive PET operating fluorescent turn-on cell permeable novel probe R1 has been successfully developed and utilized for the detection of Fe⁺³ in the pure aqueous system at sub-nanomolar level. Moreover, probe R1 demonstrate highly sensitive and selective towards Fe⁺³ over the other divalent and trivalent metal ions and was established by using fluorescence spectroscopy. The efficiency and aid of R1 was demonstrated by the fluorescence imaging of captured Fe⁺³ within Pollen grains by using fluorescence microscopy. These results indicate that, this is the first fluorescent turn-on PET probe to detect sub-nanomolar Fe⁺³ in the pure aqueous system and in cellular level.     

A retrievable and highly selective fluorescent probe for monitoring sulfide and imaging in living cells

A novel selective fluorescent chemosensor based on an 8-hydroxyquinoline-appended fluorescein derivative (L1) was synthesized and characterized. Once combined with Cu(2+), it displayed high specificity for sulfide anion. Among the various anions, only sulfide anion induced the revival of fluoresecence of L1, which was quenched by Cu(2+), resulting in "off-on"-type sensing of sulfide anion. What's more, the sensor was retrievable to indicate sulfide anions with Cu(2+), and S(2-), in turn, increased. With the addition of Cu(2+), compound L1 could give rise to a visible pink-to-yellow color change and green fluorescence quenching. The resulting yellow solution could change to pink and regenerate to green fluorescence immediately upon the addition of sulfide anion; however, no changes were observed in the presence of other anions, including CN(-), P(2)O(7)(4-), and other forms of sulfate, making compound L1 an extremely selective and efficient sulfide chemosensor. The signal transduction occurs via reversible formation-separation of complex L1Cu and CuS. What's more, the biological imaging study has demonstrated that the chemosensor can detect sulfur anions in biological systems at a relatively low concentration.     

Ratiometric and selective two-photon fluorescent probe based on PET-ICT for imaging Zn2+in living cells and tissues简

A two-photon fluorescent probe TPZn was developed for specific ratiometric imaging Zn2＋ in living cells and tissues. Significant ratiometric fluorescence change was based on photoinduced electron transfer and intramolecular charge transfer. The synthetic method of TPZn was simple. It was successfully used to selectively image Zn2＋ based on the higher binding affinity for Zn2＋ than for Cd2＋. TPZn was easily loaded into the living cell and tissues with high membrane permeability in a complex biological environment. TPZn could clearly visualize endogenous Zn2＋ by TP ratiometric imaging in hippocampal slices at a depth of 120 μm. Thus, TPZn is a useful tool to image of Zn2＋ in living cells and tissues without interference from Cd2＋.     

A NBD-based simple but effective fluorescent pH probe for imaging of lysosomes in living cells

NBDlyso with lysosome-locating morpholine moiety has been developed as a high selective and sensitive fluorescent pH probe. This probe can respond to acidic pH (2.0–7.0) in a short time (less than 1 min) and not almost change after continuously illuminated for an extended period by ultraviolet light. The fluorescence intensity of NBDlyso enhanced 100-fold in acidic solution, with very good linear relationship (R² = 0.996). The pK_a of probe NBDlyso is 4.10. Therefore, NBDlyso was used to detect lysosomal pH changes successfully. Besides, X-ray crystallography was used to verify the structure of NBDlyso, and the recognition mechanism involving photo-induced electron transfer was interpreted theoretically by means of DFT and TDDFT calculations skillfully when NBDlyso comes into play under the acidic condition. This probe showed good ability to sense pH change in living cell image.     

Highly selective two-photon fluorescent probe for imaging of nitric oxide in living cells简

A new two-photon fluorescent probe, ADNO, for nitric oxide （NO） based on intramolecular photoinduced electron transfer （PET） mechanism d/splays a rapid response to NO with a remarkable fluorescent enhancement in PBS buffer. The excellent chemoselectivity of ADNO for NO over other ROS/RNS （reactive oxygen species or nitrogen species） and common metal ions was observed. Moreover, ADNO has been successfully applied in fluorescence imaging of NO of living cells using both one-photon microscopy （OPM） and two-~hoton microscopy （TPM）,     

Developing a novel ratiometric fluorescent probe based on ESIPT for the detection of pH changes in living cells

As an important parameter of intracellular metabolism, pH plays important roles in maintaining normal physiological processes. The abnormal pH could cause disorder of cell function which may cause neurological diseases. Herein, we present two novel ratiometric fluorescent probes to detect pH changes. The probes employed 2-(2′-hydroxyphenyl)benzothiazole as fluorescent platform, and displayed desirable fluorescence response to pH on the basis of excited state intramolecular proton transfer (ESIPT) process. The probe BtyC-1 showed green fluorescence at 546 nm under acidic conditions, while it displayed strong blue fluorescence at 473 nm and weak green fluorescence at 546 nm under alkaline conditions. Biological experiments demonstrated that the probe BtyC-1 could be successfully applied for the ratiometric imaging of cellular pH and the NH₄Cl-induced pH changes in living cells.